This invention relates to novel functional ionene polymer compositions and their use. These compositions are derived from cationic polyelectrolyte structures based on ionic amine backbones. The compositions of this invention, however, additionally include various functional groups attached to this ionic amine backbone. Previously, developments in this area have been concerned with deriving novel structures solely for the benefit of the cationic nature of the resultant structure. Little attention has been paid to make-up of the groups attached to the nitrogen atoms forming the backbone of the cationic polymer structure, and these groups have consequently been confined generally to simple alkyl groups. By contrast, the novel functional ionene polymer compositions of this invention have attached to the nitrogen atoms of the polymer backbone a number of different functional groups, the characteristics of which groups result in compositions useful in a variety of ways.
Useful applications of polymeric quaternary ammonium salts have long been known in the art. U.S. Pat. No. 2,261,002 discloses a number of uses of linear polymeric quaternary ammonium compounds of the formula: ##STR1##
wherein Hal is a halogen of atomic weight at least 35; R.sup.1 is an organic radical in which the atoms adjacent to nitrogen are carbon and are attached to other atoms only by single bonds; R.sup.2, R.sup.3, and R.sup.4 are organic radicals attached to the nitrogen by carbon atoms and are so selected that not more than one of them is unsaturated; R.sup.5 and R.sup.6 are organic radicals attached to the nitrogen by carbon atoms and one of which may be unsaturated when R.sup.4 is saturated; and R.sup.1 and R.sup.4 are different organic radicals attached to the nitrogen by carbon atoms and the sum of whose chain lengths exceeds five. The uses disclosed for the polymeric quaternary ammonium compounds include, among others, their use a photographic chemicals, pesticides, pour-point depressants, pigment dispersion control agents, and surface active agents.
U.S. Pat. No. 2,271,378 discloses compounds similar to those described in U.S. Pat. No. 2,261,002; and sets out their particular use as pest control agents.
U.S. Pat. No. 3,489,663 discloses electrolytic polymerization of ethylenically unsaturated monomers by applying an electric potential while the monomer is in a liquid diluent containing a polymeric ternary or quaternary onium compound as a conducting electrolyte. A preferred class of linear polymeric quaternary onium compounds useful in the patent method are those consisting essentially of recurring units represented by the formula: ##STR2##
wherein R and R' each represent an alkyl (including cycloalkyl), aralkyl, aryl, or alkaryl radical. Another preferred class of quaternary onium compounds useful in the patent method are those consisting essentially of recurring units represented by the formula: ##STR3## wherein R represents an alkylene or aralkylene radical.
U.S. Pat. No. 3,558,314 discloses light-sensitive silver halide material containing as a sensitizer a water soluble quaternary compound having the general formula: ##STR4##
wherein Y is a radical selected from the group consisting of alkyl, phenylalkyl, hydroxyalkyl, alkoxyalkyl, acyloxyalkyl, aminoalkyl, alkylaminoalkyl, and acylaminoalkyl, the alkyl group of the radical having up to 18 carbon atoms.
U.S. Pat. No. 3,632,507 discloses a process for the flocculation of particles dispersed in aqueous media, which employs as a flocculant polymeric quaternary ammonium salts having repeating units of the general formula: ##STR5## wherein R is a lower alkyl group, particularly an alkyl group containing 1-4 carbon atoms.
U.S. Pat. No. 3,632,559 discloses cationically active, water soluble polyamides obtained by alkylation with a bifunctional alkylation agent of the formula: ##STR6## wherein each of R.sub.1 and R.sub.2 is selected from lower alkyl and lower hydroxy alkyl radicals.
U.S. Pat. No. 3,671,468 discloses polymers represented by the formula: ##STR7##
wherein R.sub.1, R.sub.2, R.sub.3, and R.sub.4 represent a lower alkyl group, or R.sub.1 and R.sub.2 and/or R.sub.3 and R.sub.4, when taken together with the nitrogen atoms to which they are attached, may form heterocyclic rings.
Canadian Pat. No. 878,585 discloses a process for preparing a water-soluble cationic polymeric polyelectrolyte which comprises reacting a particular class of dihalo organic compounds with a ditertiary amine in the presence of water. The resulting polymers are useful in a number of applications including utility as drainage aids, formation aids, retention aids, strength aids, and flocculants.
South African Pat. No. 71/5573 discloses a high molcular weight polymeric composition comprising a polymeric backbone to which is grafted an ionene type polymer by means of a coupling agent. A wide variety of uses for the compositions are described.
This invention is directed to novel functional ionene polymer compositions and to novel functional diamine intermediates useful in the preparation of the functional ionene polymer compositions.
The novel functional ionene polymer compositions of this invention may be represented by the formula: ##STR8##
wherein R is independently selected from the group CH.sub.2 and substituted CH.sub.2 groups where one of the hydrogen atoms of the group is replaced by alkyl or hydroxymethyl;
wherein Y is a member selected from the group consisting of ##STR9## --C.tbd.C--, --O--, ##STR10## --OCH.sub.2 CH.sub.2 O--, ##STR11## --OCH.sub.2 O--, --S--, --SO--, --SO.sub.2 --, and aryl;
wherein R.sub.1 represents the group: ##STR12##
where R.sub.3 is hydrogen, lower alkyl of from 1 to 4 carbon atoms, or lower alkenyl of from 1 to 4 carbon atoms; R.sub.4 is hydrogen, halogen, straight or branched alkyl, cycloalkyl, aryl, alkaryl, or aralkyl; and
where R.sub.5 is a member selected from the group consisting of: ##STR13##
where R.sub.4 has the same meaning as above;
where R.sub.6 is selected from the group consisting of straight or branched alkyl, cycloalkyl, hydroxyalkyl and alkoxyalkyl;
where R.sub.7 has the same meaning as R.sub.6, additionally including hydrogen, haloalkyl and aryl;
where R.sub.8 and R.sub.9 are each independently selected from the group consisting of hydrogen, alkyl, hydroxyalkyl, cycloalkyl, aryl, alkaryl, aralkyl, and alkoxyalkyl;
where M.sup..sym. is hydrogen ion, alkali metal ion, alkaline earth metal ion, or ammonium;
wherein R.sub.2 is a straight or branched alkyl chain of 1 to 18 carbon atoms, which may be interrupted by one or more atoms of oxygen or sulfur; aralkyl or cycloalkyl;
wherein A.sup..crclbar. is an anion; and
wherein x and y are integers from 1 to 10; and n is an integer of 2 or greater.
The functional ionene polymer compositions of this invention may be prepared, and have been found to be useful, in a wide range of molecular weights. The average molecular weight may be as low as about 300 or as high as 300,000 or more. Thus, n may be an integer of 2 to 1000 or higher. The average molecular weight of the functional ionene polymer actually employed will be determined by the requirements of the particular use to which the polymer composition is being put.